Spies Of The Civil War

Like most historic battles, the U.S. Civil War had its spies--men and women--on both sides. It was a hazardous occupation with few rewards.

Spying during the Civil War was no less hazardous for agents than at any time of armed conflict in history. Rewards and recognition were negligible on both sides, and, as often as not, information obtained at great risk was ignored by the commanders in the field.

While outcomes of the historic battles were not often determined by information obtained by spies, certainly the information, or lack of it, did have some influence, particularly in the last two years of the war.

The early spies were not held in high esteem. Prior to and during the early part of the war neither side had a formal intelligence branch, nor any thought to forming one or even training spies. Any spying to be carried out was usually done on behalf of individual generals with no regard to sharing information. Even noted railway detective Allan Pinkerton's information-- some provided by his secret agents to thwart a plot to either assassinate Abraham Lincoln or at least to forestall his inauguration, was sometimes ignored.

On the other hand, Pinkerton's people regularly over-estimated the Confederate forces arrayed against Union General George McClellan - sometimes more than ten times the actual number. In part on the basis of this erroneous information, McClellan so repeatedly refused to engage the enemy he was eventually relieved of command of the Army of the Potomac. Ironically, Pinkerton's spies, so superb at gathering raw information, were hopelessly inept at analyzing it.

Until he was captured and hanged in Richmond, the most effective of Pinkerton's agents was Timothy Webster. Webster played his pro-Confederate role so well, he was arrested in Washington as a suspected Confederate spy. His escape from custody secured him even more credibility in Confederate circles and he was eventually provided a passport to travel freely throughout Confederate territory.

When the Confederacy entered the Civil War it lacked any intelligence support even close to that provided by Pinkerton to the Union. Despite this disadvantage, Confederate operatives did have some notable successes. For example, even as Pinkerton was providing McClellan gross over-estimations of Confederate strength, an espionage ring organized by a spymaster, Thomas Conrad, in Washington provided Richmond with regular updates of McClellan's entire order of battle. At another point in the war, Conrad managed to have one of his spies on the staff of the Union's head of secret police, Lafayette Baker.

To the extent Baker was recognized for his ruthlessness, cunning and success, his Confederate counterpart, Brigadier General John Winder was reported to be incompetent, inexperienced, and susceptible to material blandishment, the last-noted often having to do with issuance of travel passes. Nor, apparently, was Winder as security conscious as might have been advisable. He had posted on his headquarters wall the order of battle of troops defending the Richmond peninsula, and at least once guards had to chase off a stranger diligently copying the lists.

The brigadier general also opened the door for one of the Union's most consistently productive spies, Elizabeth Van Lew, who in her diary emphasized how despicable, yet useful, she found his vanity.

Van Lew wore her pro-Union sympathies as openly as a corsage on her dress. She began her spying activities by gleaning information from Union prisoners of war in Richmond's Libby Prison. She devised a cipher code and used her servants, many of whom were former slaves, to act as couriers to get information through the lines to Generals Grant and Butler. So imaginative was she that managed to have one of her spies employed on the household staff of Jefferson Davis. As if in recognition of her wartime efforts, immediately after the fall of Richmond, General Grant took tea with Van Lew on her front porch in full view of the vanquished population.

Of all of the Civil War's generals, General Grant placed the most reliance on intelligence gathered by spies, so much so that he charged a brigadier general, Grenville Dodge, with setting up spy networks throughout the Confederacy. Almost reminiscent of Iran-Contra in contemporary times, Dodge used revenue from the sale of confiscated southern cotton to finance the activities of his agents.

The Confederacy was not without its prominent women spies, of whom Rose Greenhow was most notable. She was very well-connected in Washington political circles, counting among her frequent visitors, then-President James Buchanan and Henry Wilson during his term as chairman of the Senate Military Affairs Committee. Information she provided acknowledged to have been the key to Confederate success at Bull Run.

More famous than Greenhow was Belle Boyd, achieving her fame more with her own flamboyance than by the intelligence product of her exploits. Late in the war, the Union deported the pesky lady to Canada.

By the end of the Civil War the value of intelligence gathering, its timely transmission, and its accurate analysis had been well proven. The telegraph and semaphore relay systems had undergone dramatic improvement. Codes and ciphers had become much more complex and sophisticated. Certainly agents in place being provided specific direction from higher authority was recognized as far more fruitful than the "catch as catch can" fragmented approach taken by both sides early in the conflict. Indeed, never again would the United States be without an intelligence branch.